Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones via [4 + 2] imino-Diels–Alder cyclization from N-aryl-3-hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3-hydroxyisoindolinones w...

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Autores principales: Jha, Amitabh, Chou, Ting-Yi, ALJaroudi, Zainab, Ellis, Bobby D, Cameron, T Stanley
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999823/
https://www.ncbi.nlm.nih.gov/pubmed/24778740
http://dx.doi.org/10.3762/bjoc.10.81
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author Jha, Amitabh
Chou, Ting-Yi
ALJaroudi, Zainab
Ellis, Bobby D
Cameron, T Stanley
author_facet Jha, Amitabh
Chou, Ting-Yi
ALJaroudi, Zainab
Ellis, Bobby D
Cameron, T Stanley
author_sort Jha, Amitabh
collection PubMed
description The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones via [4 + 2] imino-Diels–Alder cyclization from N-aryl-3-hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3-hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl)vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
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spelling pubmed-39998232014-04-28 Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome Jha, Amitabh Chou, Ting-Yi ALJaroudi, Zainab Ellis, Bobby D Cameron, T Stanley Beilstein J Org Chem Full Research Paper The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones via [4 + 2] imino-Diels–Alder cyclization from N-aryl-3-hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3-hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl)vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed. Beilstein-Institut 2014-04-14 /pmc/articles/PMC3999823/ /pubmed/24778740 http://dx.doi.org/10.3762/bjoc.10.81 Text en Copyright © 2014, Jha et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Jha, Amitabh
Chou, Ting-Yi
ALJaroudi, Zainab
Ellis, Bobby D
Cameron, T Stanley
Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
title Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
title_full Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
title_fullStr Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
title_full_unstemmed Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
title_short Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
title_sort aza-diels–alder reaction between n-aryl-1-oxo-1h-isoindolium ions and tert-enamides: steric effects on reaction outcome
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999823/
https://www.ncbi.nlm.nih.gov/pubmed/24778740
http://dx.doi.org/10.3762/bjoc.10.81
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